1,4'-Bipiperidine → 1-Cyclopropyl-7-fluoro-9-methyl-4-oxo-8-[4-(1-piperidyl)-1-piperidyl]quinolizine-3-carboxylic acid

HRID 1879

Reaction equation

HRID 1879 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:19])=[C:11](Cl)[C:12]([F:17])=[CH:13]2)=[C:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=1)=[O:5])C.[N:23]1([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(#N)C>[N:23]1([CH:29]2[CH2:34][CH2:33][N:32]([C:11]3[C:12]([F:17])=[CH:13][N:14]4[C:9]([C:10]=3[CH3:19])=[C:8]([CH:20]3[CH2:22][CH2:21]3)[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[C:15]4=[O:16])[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 786071,4'-BipiperidineHCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 4885321-Cyclopropyl-7-fluoro-9-methyl-4-oxo-8-[4-(1-piperidyl)-1-piperidyl]quinolizine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 70 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 4-(1-piperidyl)piperidine (70 mg, 0.4 mmol, Aldrich Chem. Co.), and carried forward as described in Example 253j-k to give the title product. MS 428 (M+H)+ ; 1H NMR (CDCl3) ∂: 0.69 (m, 2H), 1.02 (m, 2H), 1.18 (m, 4H), 2.27 (n, 1H), 2.78 (s, 3H), 2.72 (m, 1H), 3.35 (m, 3H), 3.55 (m, 1H), 3.75 (m, 1H), 8.36 (s, 1H), 9.20 (d, 1H). Anal. Calcd for C24H30 N3O3F.1.5 H2O: C, 63.42; H, 7.32; N, 9.24; Found: C, 62.99; H, 7.04; N, 8.78.

Sources & evidence

ORD record
ord-021e1069b0ae4865bfe08ff43a38ea27
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Linked notes

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